Trifluoroacetic acid → 2-(4-(Methoxycarbonyl)-2-methylphenyl)acetic acid

HRID 220828Notes

Reaction equation

HRID 220828 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[C:13]([CH3:25])[CH:12]=1>ClCCl>[CH3:8][O:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[C:13]([CH3:25])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 575554334-Tert-butoxycarbonylmethyl-3-methyl-benzoic acid methyl ester

Product 1

HCID 575552242-(4-(Methoxycarbonyl)-2-methylphenyl)acetic acidYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 ml) was added to a solution of 4-tert-butoxycarbonylmethyl-3-methyl-benzoic acid methyl ester from Example E32.1 (2.84 g, 10.7 mmol) in dichloromethane (15 ml). The mixture was stirred for 90 min at room temperature, concentrated in vacuo and azeotroped with toluene. The residue was recrystallised from EtOAc and hexane to yield the title compound (1.81 g, 81%).

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with toluene
  3. customThe residue was recrystallised from EtOAc and hexane

Sources & evidence

ORD record
ord-40ffc1f9c1c244aa81ff6b3c5a9e1bdd
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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